Reactions of lead (IV). Part XXIV. Reactions with some benzenoid compounds in the presence of monomethyl oxalate

Abstract

Benzene undergoes methoxycarbonylation and methylation, and anisole these reactions as well as acetoxylation and oxidative dimerisation, when treated with lead tetra-acetate in the presence of monomethyl oxalate. Evidence is adduced that radical-chain reactions are involved in the formation of each type of product, that the methoxycarbonyl radical mediates in methoxycarbonylation, and that oxidative dimerisation occurs by electrophilic plumbylation followed by radical-chain processes.